Results
Title

Alkylammonium Guest Induced-Fit Recognition by a Flexible Dihomo­oxacalix[4]arene Derivative.

Authors

Talotta, Carmen; Gaeta, Carmine; De Rosa, Margherita; Ascenso, José R.; Marcos, Paula M.; Neri, Placido

Abstract

The conformationally mobile tetramethoxy-dihomooxacalix[4]arene 1c is able to interact with linear and branched alkylammonium guests through an induced-fit process mainly driven by H-bonds and cation-π interactions. Although free 1c adopts a 1,4-alternate conformation in solution, in the presence of linear nBuNH3 and branched sBuNH3 and iPrNH3 guests, it preferentially forms endo-complexes in a cone conformation through adaptive structural change in response to the presence of the ammonium guests. In accordance with previous results, the DFT-optimized structures of the complexes indicate that they are mainly stabilized by H-bonding interactions between the guest ammonium group and the host CH2OCH2 ethereal bridge.

Subjects

AMMONIUM compounds; CATIONS synthesis; HYDROGEN bonding; PROTEIN conformation; OXALIC acid

Publication

European Journal of Organic Chemistry, 2016, Vol 2016, Issue 1, p158

ISSN

1434-193X

Publication type

Academic Journal

DOI

10.1002/ejoc.201501319